Potassium Hydroxide → 3-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrile

HRID 22368

Reaction equation

HRID 22368 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22].[OH-].[K+]>O1CCCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:3][C:1]#[N:2])=[CH:15][C:14]=1[C:21]([F:22])([F:23])[F:24]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 1186424-Chloro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 541762263-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution consisting of 10.6 g (0.06 mol) of diethyl cyanomethylphosphonate and 12.5 g (0.06 mol) of 4-chloro-3-trifluoromethylbenzaldehyde in 65 ml of tetrahydrofuran is added dropwise to a suspension of 6.7 g (0.12 mol) of powdered potassium hydroxide in 185 ml of tetrahydrofuran. During this process, there is a slight evolution of heat. Subsequently, the mixture is stirred at room temperature for 20 minutes and the solid material which separates off is filtered off and washed with tetrahydrofuran. The filtrate is concentrated in vacuo and the remaining residue is dried. 12.1 g (87.0% of theory) of 4-chloro-3-trifluoromethyl-cinnamonitrile are obtained as an E/Z isomeric mixture.

Workup

  1. temperatureof heat
  2. filtrationis filtered off
  3. washwashed with tetrahydrofuran
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe remaining residue is dried

Sources & evidence

ORD record
ord-d4caff9d09254cf9a804c28ae2cf88db
Source dataset
uspto-grants-1995_06
Patent number
US05428049

Linked notes

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